Why Jamaica Should Be Your Next Unexpected Caribbean Escape

I am unabashedly the opposite of a fly-and-flop traveler. Find me trying to hike a rocky shore or signing up for a half-day food tour after I land. This is precisely the reason why I was so looking forward to traveling to Jamaica, especially for an immersive travel education. I was interested to learn more about the experiences beyond the beach, and what I learned surprised me more than I thought. Let me show you the Jamaica your beach-loving friends didn’t mention.

First stop: Half Moon in Montego Bay, located only 15 minutes from the airport, has something for everyone. The resort is a hub of activity and dining accommodations, which gives it that familiar feel of an all-inclusive, but with that luxury touch. Founder’s Cove has old-world charm with approachable and spacious beachfront rooms. The Eclipse development is more modern, with accommodations surrounded by lush greenery and direct access to the infinity pool. The villas feel extra special for a group of friends or a multi-gen family. No matter where you stay, you have access to their intimate, cozy stretch of beach that feels like you’re on a private island.

Spend time at the equestrian center with Trina, who not only leads rides but is also involved in horse rescue efforts. If you need a workout, Trudy, who runs the newly renovated fitness studio, is so passionate, you will happily obey her commands. Her HIIT class left me sweaty and energized. My favorite activity: taking a peaceful, early morning bike ride around the expansive property before a seaside breakfast at Hayward’s. Whether you’re into swimming with horses, golfing, spa days, or simply lounging by the three pools, Half Moon checks all the boxes. Families will love the kids’ village and food lovers will be happy dining at 13 food and beverage options. Don’t miss out on the flaming brochette at Sugar Mill Restaurant—a memorable culinary moment.

My next stop took me to Round Hill Hotel and Villas. About 30 minutes from MBJ Airport, Round Hill is a magical property with rolling hills and a deep history. Each villa has its own special story, whether it’s an iconic filming location (How Stella Got Her Groove Back) or graced by a political dynasty (JFK and Jackie’s honeymoon spot). Many staff have long tenures at the villas and hotels and greet guests with a heartfelt “Welcome home.” It’s not just lip service—it sets the tone for the entire stay.

Put the complimentary glass-bottom boat tour at Round Hill on your list and spend time with Captain Akeem to learn about the marine ecosystem. The atmosphere blends British heritage with Jamaican spirit—you’ll see it in the design details, staff uniforms, and even the flavors on your plate. From the manager’s hosted cocktail hour at Hanover Terrace to the in-villa breakfast to having a beef pastry and the tandoori shrimp salad poolside, the food and beverage is divine. Round Hill is ideal for weddings, honeymooners, and families who wish for a more elevated stay. The kids' club is included (wow!), with options for extra care. This is the place for you if you are interested in having a beach backdrop with a little bit of glamor, charm, and discretion.

The biggest takeaway for me: Don’t treat this destination like an all-inclusive or a typical resort experience. Chat with the staff, ask questions about their experience, notice the legacy in your surroundings, and slow down on island time. You’ll find yourself wanting to come back year after year for the shortbread pineapple cookies at Round Hill, just like Ralph Lauren.

Low season is from May to September, and it's a great time to take advantage of the pricing. Holiday timing and competing with repeat guests who book months in advance may be a challenge.

For more inspiration and insider recommendations, visit our Jamaica page.